Water → HCID 25206414, compound

HRID 1947777Notes

Reaction equation

HRID 1947777 reaction equation
[CH:1]([NH:4][C:5]([CH:7]1[C:15]2[C:10](=[CH:11][C:12]([Cl:35])=[C:13]([NH:16][C:17]([C:19]3[N:20]([C:28]4[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][N:29]=4)[N:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=3)=[O:18])[CH:14]=2)[CH2:9][CH:8]1O)=[O:6])([CH3:3])[CH3:2].C(N(S(F)(F)[F:43])CC)C.O>ClCCl>[CH:1]([NH:4][C:5]([CH:7]1[C:15]2[C:10](=[CH:11][C:12]([Cl:35])=[C:13]([NH:16][C:17]([C:19]3[N:20]([C:28]4[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][N:29]=4)[N:21]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:23]=3)=[O:18])[CH:14]=2)[CH2:9][CH:8]1[F:43])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 25206573HCID 25206573, compound

Product 1

HCID 25206414HCID 25206414, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chloro-2-hydroxy-6-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-indane carboxylic acid isopropylamide (100 mg, 0.18 mmol) in dichloromethane is cooled to 0° C., treated with diethylaminosulfurtrifluoride (29 mg, 1.8 mmol), stirred for 2 hours, and treated with water. Organic layer is separated, dried over sodium sulfate, filtered, and evaporated. Purification by chromatography using ethyl acetate/hexane as eluent gives 5-chloro-2-fluoro-6-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-indane carboxylic acid isopropylamide as solid; LC/MS: 542/544 (M+1)+; m.p.: 98-99° C.

Workup

  1. customOrganic layer is separated
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by chromatography

Sources & evidence

ORD record
ord-9924cf62680f43f88a43b2515e95c3f2
Source dataset
uspto-grants-2013_03
Patent number
US08399490B2

Reaction notes

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